Natural Product: NPC264470

Natural Product IDNPC264470
Common Name
?
The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
 Azulene
IUPAC Name azulene
Synonyms
Synthetic Gene Cluster n.a.
ChEMBL Identifier CHEMBL3272628
PubChem CID 9231
Chemical Classification
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002837] Hydrocarbons
      • [CHEMONTID:0004475] Unsaturated hydrocarbons
        • [CHEMONTID:0002838] Olefins
          • [CHEMONTID:0002840] Cyclic olefins
            • [CHEMONTID:0000290] Azulenes

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

  Chemical Representations

Standard InCHIKey CUFNKYGDVFVPHO-UHFFFAOYSA-N
Standard InCHI InChI=1S/C10H8/c1-2-5-9-7-4-8-10(9)6-3-1/h1-8H
SMILES c1ccc2c(cc1)ccc2

  Calculated Properties

Physi-Chem Properties

Molecular Weight:   128.06 Volume:   151.221
?
Van der Waals volume.
Dense:   0.847 LogP:   3.457
?
The logarithm of the n-octanol/water distribution coefficients.
logD7.4:   3.368
?
The logarithm of the n-octanol/water distribution coefficient at pH=7.4.
 LogS:   -3.685
?
The logarithm of aqueous solubility value.
Rotatable Bonds:   0.0 Rigid Bonds:   11.0
TPSA:   0.0
?
Topological Polar Surface Area.
 H-Bond Acceptor:   0.0
H-Bond Donor:   0.0 Rings:   2.0
Heavy Atoms:   0.0

MedChem Properties

QED Drug-Likeness Score:   0.511 GASA:   0.0
?
GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:   1.0 Fsp3:   0.0
MCE-18:   8.0
?
MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.
 Lipinski Rule-of-5:   Rejected
Pfizer Rule:   Accepted GSK Rule:   Rejected
Golden Triangle Rule:   Accepted BMS Rule:   0
Chelating Alert:   0 PAINS Alert:   1
Colloidal aggregators:   0.057 Fluc inhibitor:   0.539
?
The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:   0.081
?
The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1
 Green fluorescence:   0.001
?
The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:   1.0 Promiscuous compounds:   0.667

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:   -4.233 MDCK Permeability:   -4.485
Pgp-inhibitor:   0.159 Pgp-substrate:   0.38
PAMPA:   0.303
?
The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).
 Human Intestinal Absorption (HIA):   0.006
20% Bioavailability (F20%):   0.03 30% Bioavailability (F30%):   0.227
50% Bioavailability (F50%):   0.544

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):   0.807 MRP1:   0.73
Plasma Protein Binding (PPB):   97.295% Volume Distribution (VD):   0.053
Fu: 2.37%
?
The fraction unbound in plasms.
 OATP1B1 inhibitor:   0.876
OATP1B3 inhibitor:   0.923 BCRP inhibitor:   0.77
BSEP inhibitor:   0.928

ADMET: Metabolism

CYP1A2-inhibitor:   0.107 CYP1A2-substrate:   0.957
CYP2C19-inhibitor:   0.694 CYP2C19-substrate:   0.861
CYP2C9-inhibitor:   0.905 CYP2C9-substrate:   0.369
CYP2D6-inhibitor:   0.584 CYP2D6-substrate:   0.235
CYP3A4-inhibitor:   0.302 CYP3A4-substrate:   0.996
CYP2B6-substrate:   0.963 CYP2C8-inhibitor:   0.994
HLM stability:   0.997
?
Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):  9.042 Half-life (T1/2):  1.924

ADMET: Toxicity

hERG Blockers:  0.194 hERG Blockers (10um):  0.615
Human Hepatotoxicity (H-HT):  0.593 Drug-induced Liver Injury (DILI):  0.418
AMES Toxicity:  0.678 Rat Oral Acute Toxicity:  0.394
Maximum Recommended Daily Dose:  0.336 Skin Sensitization:  0.564
Carcinogencity:  0.759 Eye Corrosion:  0.921
Eye Irritation:  0.993 Respiratory Toxicity:  0.576
Drug-induced Neurotoxicity:  0.767 Ototoxicity:  0.207
Hematotoxicity:  0.352 Drug-induced Nephrotoxicity:  0.385
Genotoxicity:  0.244 RPMI-8226 Immunitoxicity:  0.052
A549 Cytotoxicity:  0.119 Hek293 Cytotoxicity:  0.235
BCF:   2.178
?
Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].
 IGC50:   3.532
?
48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:   4.191
?
48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].
 LC50FM:   4.049
?
96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. rhizome n.a. DOI[10.1021/np100392m]
NPO22051 Litsea verticillata Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[12762792]
NPO12907 Hypericum carinatum Species Hypericaceae Eukaryota n.a. n.a. n.a. PMID[15921431]
NPO29016 Valeriana jatamansi Species Caprifoliaceae Eukaryota n.a. n.a. n.a. PMID[19245261]
NPO29016 Valeriana jatamansi Species Caprifoliaceae Eukaryota n.a. n.a. n.a. PMID[20151678]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota n.a. n.a. n.a. PMID[20476749]
NPO29016 Valeriana jatamansi Species Caprifoliaceae Eukaryota n.a. n.a. n.a. PMID[20853876]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[20879743]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[21807513]
NPO5681 Acorus gramineus Species Acoraceae Eukaryota n.a. rhizome n.a. PMID[21936523]
NPO5681 Acorus gramineus Species Acoraceae Eukaryota Rhizomes n.a. n.a. PMID[21936523]
NPO3123 Anthemis cretica Species Asteraceae Eukaryota n.a. aerial part n.a. PMID[22351977]
NPO5681 Acorus gramineus Species Acoraceae Eukaryota rhizomes n.a. n.a. PMID[22951040]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota n.a. rhizome n.a. PMID[23713285]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. root n.a. PMID[23738470]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. rhizome n.a. PMID[23738470]
NPO18068 Curcuma phaeocaulis Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[23755850]
NPO29083 Matricaria chamomilla Species Asteraceae Eukaryota n.a. flower n.a. PMID[25051625]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[25275213]
NPO6701 Cinnamomum camphora Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[25612070]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota rhizomes n.a. n.a. PMID[26296476]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota n.a. n.a. n.a. PMID[26305406]
NPO6879 Laetia corymbulosa Species Salicaceae Eukaryota Bark n.a. n.a. PMID[28290698]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota Rhizomes n.a. n.a. PMID[29116780]
NPO6701 Cinnamomum camphora Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[31994661]
NPO6701 Cinnamomum camphora Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[32035880]
NPO6701 Cinnamomum camphora Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[32674448]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota n.a. n.a. n.a. PMID[32807141]
NPO6701 Cinnamomum camphora Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[34500567]
NPO29016 Valeriana jatamansi Species Caprifoliaceae Eukaryota n.a. n.a. n.a. PMID[35481430]
NPO24416 Artemisia tournefortiana Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[35508595]
NPO57430 Artemisia khorassanica Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[35508595]
NPO6701 Cinnamomum camphora Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[36770639]
NPO29083 Matricaria chamomilla Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[36840093]
NPO25014 Achillea millefolium Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[36905473]
NPO6701 Cinnamomum camphora Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[37533252]
NPO62703 Micromeria madagascariensis Genus Lamiaceae Eukaryota n.a. n.a. n.a. PMID[38434328]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota n.a. n.a. n.a. PMID[38821245]
NPO6701 Cinnamomum camphora Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[38998569]
NPO29083 Matricaria chamomilla Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[39125862]
NPO6701 Cinnamomum camphora Species Lauraceae Eukaryota n.a. n.a. n.a. PMID[39489989]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[9868158]
NPO6701 Cinnamomum camphora Species Lauraceae Eukaryota n.a. stem n.a. Database[Article]
NPO13840 Streptomyces incarnatus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[COCONUT]
NPO29083 Matricaria chamomilla Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO25014 Achillea millefolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO18068 Curcuma phaeocaulis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO5681 Acorus gramineus Species Acoraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17203 Impatiens siculifer Species Balsaminaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO6701 Cinnamomum camphora Species Lauraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO24416 Artemisia tournefortiana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO19748 Aspergillus phoenicis Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO10235 Castanopsis eyrei Species Fagaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20253 Eucalyptus decorticans Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO21477 Euryops rupestris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12656 Holarrhena febrifuga Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO12907 Hypericum carinatum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO11665 Kloeckera brevis n.a. n.a. n.a. n.a. n.a. n.a. Database[COCONUT]
NPO6879 Laetia corymbulosa Species Salicaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO22051 Litsea verticillata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO28772 Polygonum mite Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20180 Rabdosia loxothyrsa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO17743 Solanum aculeatum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO20602 Trichomanes reniforme Species Hymenophyllaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO13857 Mentha canadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO29016 Valeriana jatamansi Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO31056 Mentha haplocalyx Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO3123 Anthemis cretica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[COCONUT]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25014 Achillea millefolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6701 Cinnamomum camphora Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO31056 Mentha haplocalyx Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5681 Acorus gramineus Species Acoraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29083 Matricaria chamomilla Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12656 Holarrhena febrifuga Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17203 Impatiens siculifer Species Balsaminaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22051 Litsea verticillata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6701 Cinnamomum camphora Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO13857 Mentha canadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25014 Achillea millefolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5681 Acorus gramineus Species Acoraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29083 Matricaria chamomilla Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12656 Holarrhena febrifuga Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22051 Litsea verticillata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6879 Laetia corymbulosa Species Salicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17203 Impatiens siculifer Species Balsaminaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3123 Anthemis cretica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6701 Cinnamomum camphora Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22051 Litsea verticillata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29083 Matricaria chamomilla Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25014 Achillea millefolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO31056 Mentha haplocalyx Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18068 Curcuma phaeocaulis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO5681 Acorus gramineus Species Acoraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO13857 Mentha canadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29016 Valeriana jatamansi Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO20180 Rabdosia loxothyrsa Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6701 Cinnamomum camphora Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19748 Aspergillus phoenicis Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22051 Litsea verticillata Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3123 Anthemis cretica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29016 Valeriana jatamansi Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11665 Kloeckera brevis n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO24416 Artemisia tournefortiana Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10235 Castanopsis eyrei Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25014 Achillea millefolium Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21477 Euryops rupestris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13840 Streptomyces incarnatus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO17743 Solanum aculeatum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12907 Hypericum carinatum Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20253 Eucalyptus decorticans Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13857 Mentha canadensis Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6879 Laetia corymbulosa Species Salicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28772 Polygonum mite Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO20602 Trichomanes reniforme Species Hymenophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12656 Holarrhena febrifuga Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18068 Curcuma phaeocaulis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17203 Impatiens siculifer Species Balsaminaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8666 Acorus tatarinowii Species Acoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].



  NP Quantity Composition/Concentration

Organism ID Organism Name Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference
NPO24416 Artemisia tournefortiana Oil n.a. 1.67 n.a. n.a. % PMID[35508595]
NPO57430 Artemisia khorassanica Oil n.a. 3.115 n.a. n.a. % PMID[35508595]
NPO62703 Micromeria madagascariensis Oil n.a. 3.28 n.a. n.a. % PMID[38434328]

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].



 Biological Activity

Molecular-level activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference

In vitro activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT1045 Cell line U2OS Homo sapiens Activity = 104.0 % PMID[26964674]
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 Activity = 76.0 % PMID[26964674]

In vivo activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference





 Experimental ADME

Experiment Model Experiment Tissue ADME Type ADME Relation ADME Value ADME Unit Reference





 Experimental Toxicity

Quantitative toxicity

Experiment Model Experiment Organism Toxicity Type Toxicity Relation Toxicity Value Toxicity Unit Reference
- Rattus norvegicus LD50 > 4000.0 mg/kg ToxVal
- Mus musculus LD50 = 3.074376182 mg/kg TOXRIC
- Mus musculus LD50 > 3000.0 mg/kg ToxVal

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity Carcinogenicity Mutagenicity Cardiotoxicity Respiratory Toxicity Eye Irritation Endocrine Disruption
Hepatotoxicity Carcinogenicity Mutagenicity Cardiotoxicity Respiratory Toxicity Eye Irritation Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]


  Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

●  The left chart: Distribution of similarity level between NPC264470 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.5 or Top200).

Similarity Score Similarity Level Natural Product ID
0.9091 High Similarity NPC113670
0.5263 Remote Similarity NPC267443

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC264470 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.9091 High Similarity NPD675 Discontinued

Bioactivity similarity

  Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data